Search Vacation Homes in Cape Anne

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Dec 19 - Dec 21
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Jan 9 - Jan 11
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Feb 6 - Feb 8

Our top choices for Cape Anne vacation homes

Exterior
Charming Coastal/Country Home w/3 Acres & Sauna!

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$248 nightly
The price is $263
Dec 21 - Dec 22
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$286 nightly
The price is $316
Jan 4 - Jan 5, 2026
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$208 nightly
The price is $220
Dec 14 - Dec 15
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$364 nightly
The price is $402
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$285 nightly
The price is $324
Dec 14 - Dec 15
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$496 nightly
The price is $529
Dec 16 - Dec 17
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
Dining
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$494 nightly
The price is $563
Dec 14 - Dec 15
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Smart TV
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$374 nightly
The price is $426
Dec 14 - Dec 15
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Smart TV, books
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Vacation Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
$339 nightly
The price is $359
Dec 17 - Dec 18
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
$460 nightly
The price is $520
Dec 14 - Dec 15
Total with taxes and fees
Cute bungalow blocks to Stadium
Outdoor dining
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Stevensville

New! Stylish downtown home w/awesome outdoor area!
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
$475 nightly
The price is $503
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
TV, books, offices
Holly Hill Haven - Sleeps 10

Vacation Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$487 nightly
The price is $520
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Smart TV, fireplace, foosball, table tennis
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$423 nightly
The price is $482
Dec 16 - Dec 17
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Vacation Home in Historic District

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$617 nightly
The price is $703
Dec 15 - Dec 16
Total with taxes and fees
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Beach nearby, sun loungers, beach towels
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$484 nightly
The price is $552
Dec 19 - Dec 20
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Vacation Home in Edgewater

Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$591 nightly
The price is $637
Jan 5 - Jan 6, 2026
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
Pool
Family Beach House: Spacious Deck, Grill & Views

Vacation Home in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$455 nightly
The price is $480
Jan 12 - Jan 13, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Vacation Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
$366 nightly
The price is $388
Dec 14 - Dec 15
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Fridge, microwave, oven, stovetop
Golden Anchor Retreat; Lux Living! - Sleeps 7

Vacation Home in Edgewater

Golden Anchor Retreat; Lux Living! - Sleeps 7
10.0 out of 10, Exceptional, (2)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
$552 nightly
The price is $589
Dec 16 - Dec 17
Total with taxes and fees
Golden Anchor Retreat; Lux Living! - Sleeps 7
Beach
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Vacation Home in Edgewater

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
10.0 out of 10, Exceptional, (3)
"Yes, everything was over the top."
United States
Abigail B.
$312 nightly
The price is $356
Dec 14 - Dec 15
Total with taxes and fees
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cape Anne Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Cape Anne

Cape Anne Vacation Homes information

Number of reviews
273
Accommodation
611 Vacation Homes
Lowest Price
$220
Highest Price
$703

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